Bromine → HCID 71650844, compound

HRID 2220061Notes

Reaction equation

HRID 2220061 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10](=[O:19])[CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[N:13]=3)=[CH:9][C:4]=2[O:3][CH2:2]1.[Br:20]Br>C(O)(=O)C>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10](=[O:19])[CH:11]([Br:20])[C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[N:13]=3)=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

4

Reactant 2

HCID 24408BromineHCID 688850001-(1,3-benzodioxol-5-yl)-2-(6-methyl-2-pyridinyl)Ethanone

Product 1

HCID 71650844HCID 71650844, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a solution of 1-benzo[1,3]dioxol-5-yl-2-(6-methyl-pyridin-2-yl)-ethanone of Step B (2 g, 7.83 mmol) in acetic acid (15 mL) was slowly added a solution of bromine (0.40 mL, 1 equiv) in acetic acid (5 mL). The resulting reaction mixture was stirred at ambient temperature for 1 h, concentrated in vacuo, diluted with diethyl ether (20 mL) and methylene chloride (10 mL). The resulting suspension was stirred at ambient temperature for 16 hours, and then filtered to yield the title compounds as a light beige solid (3.0 g, 92%).

Workup

  1. customThe resulting reaction mixture
  2. concentrationconcentrated in vacuo
  3. additiondiluted with diethyl ether (20 mL) and methylene chloride (10 mL)
  4. stirringThe resulting suspension was stirred at ambient temperature for 16 hours
  5. filtrationfiltered

Sources & evidence

ORD record
ord-aad80296f11e48b7bc757e52e77bbb67
Source dataset
uspto-grants-2008_08
Patent number
US07417041B2

Reaction notes

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